Pyridine!

I remember at one point having a (review?) paper called “Pyridine!” in my collection. Love that title. I can’t remember who wrote it, what year it was from or what it contained. Now I can’t find it again, because SciFinder and Google Scholar seem to ignore the exclamation mark in text based searches. If you know of a workaround or how else to rediscover this article, please tell me.

Anyways, pyridines and pyridones lie close to my heart, and I am delighted to see the latest progress in synthesis of highly substituted pyridines. I think it was Manfred Schlosser, the crowned King of pyridines, who coined the term “regioexhaustive functionalizations”, which I try to reuse as often as possible.

During this fall in Organic Letters alone there appear at least three excellent papers on the topic.

Normally, I would paste the graphical abstracts here, but as time is not on my side right now, you will have to suffice with uncovering these manually – this time only. I can however vouch for the awesomeness of all three, if you are at all into heterocyclic chemistry.

Finally, I would like reveal my hidden agenda and turn your attention and this post into a blatant plug for one of our own publications. Ha! We were the first to synthesize pyridines substituted with five different elements (1 and 2).

3 Responses to Pyridine!

the treatment of pyridine 2 with m-CPBA you will get you sulfoxide and then immediately the sulfone. You would have to beat much harder on it to get it all the way to N-oxide-sulfone.

There is a lovely preparation where you oxidize 2-methylthio-4,6-dichloropyrimidine with mCPBA to the Me-sulfone (without harming the ring nitrogens and then you displace the produced methylsulfone in 2-position with a (poorly reactive) amine under mild conditions, this substitution leaves the two chlorines unmolested.